Duke vs. Yale: The Preppiest NCAA Tournament Matchup of All-Time?

Duke held off UNC-Wilmington. Yale upset No. 5 seed Baylor. The two schools will meet in the (now appropriately named) second round. This matchup begs an obvious question: is this the preppiest NCAA Tournament pairing of all time?

We can say with conviction this is the preppiest matchup of 2016. Both schools exude a particular stereotype: gingham, polos, boat shoes, privilege, guys named Chase, Tad, or the equivalent. Basically entire schools populated by 1980s high school movie villains. The difference: Yale students, perhaps, had a better ACT score, one more extracurricular activity, or slightly more important parents.

Historically, there is a shallow pool of prep on prep matchups. “Sports” at many preppy schools means lacrosse or an active club Quidditch scene. Dartmouth and Middlebury have combined for zero NCAA Tournament appearances. But, there are a few notable exceptions.

Georgetown had perhaps the preppiest tournament run in 1989. The Hoyas played Princeton, Notre Dame, and Duke en route to the Elite Eight. They put up a solid effort with Vanderbilt and Boston College heading to the Final Four in 2007.

Vanderbilt played Georgetown in 1991 and Harvard in 2012. Pepperdine played Duke in 1985. College of Charleston and Princeton have, for the most part, ducked fellow preppy schools.

However, the one game that gives Duke vs. Yale a run came in 1995, under similar circumstances. No. 4 seed University of Virginia blew out Nicholls State. No. 12 seed Miami of Ohio upset Arizona. The two met in the second round in the Midwest Regional. Virginia won 60-54.

Was that game preppier than Duke vs. Yale? It’s a tough call.

From a style perspective, it’s hard to top UVA and Miami of Brohio. Both exude a pure, concentrated preppy. But, to be truthful, it’s an aspirational preppiness. Both schools imitate the true upper crust traditions and undue privilege one would find in the Northeast or, specifically, at Yale.

Yale was preppy before it was a term. Whatever Duke lacks by being founded after the United States, it more than makes up for in general smugness and odiousness. Duke vs. Yale will be the preppiest tournament matchup of all time. The tension at Wall Street firms today will be palpable.